Cesium carbonate → 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide
Reaction equation
N1(CCS(N2CCC(C3[C:25]4[C:20](=[C:21]([C:31](N)=[O:32])[CH:22]=[C:23](C5C=CSC=5)[CH:24]=4)NC=3)CC2)(=O)=O)CCCC1.Br[C:35]1[CH:36]=[C:37]2[C:41](=[C:42]([C:44]([NH2:46])=[O:45])[CH:43]=1)[NH:40][CH:39]=[C:38]2[CH:47]1[CH2:52][CH2:51][N:50]([S:53]([CH2:56][CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])(=[O:55])=[O:54])[CH2:49][CH2:48]1.OCC1C=C(B(O)O)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:60][N:59]([CH3:61])[CH2:58][CH2:57][CH2:56][S:53]([N:50]1[CH2:49][CH2:48][CH:47]([C:38]2[C:37]3[C:41](=[C:42]([C:44]([NH2:46])=[O:45])[CH:43]=[C:35]([C:25]4[CH:24]=[CH:23][CH:22]=[C:21]([CH2:31][OH:32])[CH:20]=4)[CH:36]=3)[NH:40][CH:39]=2)[CH2:52][CH2:51]1)(=[O:55])=[O:54]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared following the general procedure described in intermediate 16. Thus, 5-bromo-3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (150 mg, 0.32 mmol), [3-(hydroxymethyl)phenyl]boronic acid (195 mg, 1.27 mmol), Pd(PPh3)4 (31 mg, 10%) and cesium carbonate (220 mg, 0.64 mmol) were reacted to form the desired product which was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to yield the desired product (230.0 mg, 36%).
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-bd7e866203894a1a9680b38e2b74d4b7
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858796B2
Reaction notes
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